p-Toluenesulfonic acid → 4,4'-Dibromotriphenylamine

HRID 571023

Reaction equation

HRID 571023 reaction equation
[CH:1]1[C:6]([NH:7][C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)=[CH:5][CH:4]=[C:3]([Br:15])[CH:2]=1.[C:16]1(=O)[CH2:21][CH2:20][C:19](=O)[CH2:18][CH2:17]1.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH:16]1[CH:21]=[CH:20][C:19]([N:7]([C:8]2[CH:13]=[CH:12][C:11]([Br:14])=[CH:10][CH:9]=2)[C:6]2[CH:1]=[CH:2][C:3]([Br:15])=[CH:4][CH:5]=2)=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 125111,4-CyclohexanedioneHCID 629950Bis(4-bromophenyl)amine

Product 1

HCID 135947074,4'-DibromotriphenylamineYield 67%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 4,4′-dibromodiphenylamine (7.3 g. 22 mmol), cyclohexane-1,4-dione (2.5 g., 23.3 mole), para-toluenesulfonic acid (0.1 g.), and toluene (100 mL) was kept at reflux with a Dean-Stark 15 phase separator containing 4A molecular sieves. After 18 hours at reflux, the reaction was diluted with toluene, and the toluene solution was washed with water, dried, and concentrated. The residue was dissolved in hexanes, and the hexanes solution was then passed through a column of silica gel to afford 4,4′-dibromotriphenylamine as a colorless glass, 5.04 g., 67% yield. Mass Spec (m/z): 401, 403, 405 (M+).

Workup

  1. temperatureat reflux with a Dean-Stark 15 phase separator
  2. temperatureAfter 18 hours at reflux
  3. washthe toluene solution was washed with water
  4. customdried
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in hexanes

Sources & evidence

ORD record
ord-bdf96a7afd554b108fcf9d56789309d2
Source dataset
uspto-grants-2015_05
Patent number
US09024037B1

Linked notes

Loading…